When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age.
Dan and I used to go mess around everyday. His parents worked from early in the morning to around six to seven in the evening. One day we were out messing around way out in a pasture and came across a pond that had a small dock on it. It was hot so we decided to take a swim. Dan started to get undressed down to his underwear and I followed suit. We jumped in and swam around a while before we got out. When we got out our tighty-whitees were see through. I was looking at Dan's cock and realised how large it was. I looked up and he was looking at me and pulled his cock out and shook it and laughed, I did the same. We started laughing as we shook our cocks at each other. His started to get hard and I commented on how big it was. He said "yea it's a big ole dick huh?" I said "hell yea and you got hair too!"
Dan started to stroke his cock and he looked at me and said, "you want to touch it?" "No", I said. "Come on, feel how soft the hair is". I reached over and felt the soft hair then he slapped his cock against my hand making me jump a bit. His cock was completely hard probably 6" or a little bigger. He looked at me and said, "go ahead, touch it". I reached over and touched the head, it was soft but yet firm. I slowly wrapped my hand around it and stroked it a couple times when he reached over and grabbed my cock and started to stroke it as well.
Dan looked at me and said "I'll suck yours if you suck mine". I wasn't sure what to say or do about this. Dan leaned close to me and licked the head of my small cock and sucked in and out of his mouth a couple times.
"Feels good doesn't it?" he said.
"Yea it does" I told him.
"You go ahead and suck mine for a while then I'll suck yours" he told me.
"Ok", so I leaned over as he laid back and pulled his underwear off. I slowly started licking the head and sucking his cock. It really felt strange to be doing this, but also sort of exciting. I sucked his cock for probably 10 minutes or so when I felt his body start to wiggle and his breathing was short.
"Do you want me to stop?" I asked him.
"Oh no keep going, it feels really good" he said to me.
"Ok, just tell me when your going to cum" I told him.
"Ok, I will" he said to me.
I slid his hard cock back inn my mouth and started sucking him again. This time he kept pushing my head down until I would gag bit. I would come up, take a few big breaths and slide his cock back in my mouth. I started sucking faster and stroking his cock taking as much as I could in my mouth without gagging. All of a sudden Dan grabbed the back of my head and held it down as his hips bucked up. I felt the hot shot of his cum hitting the back of my throat and then flooding my mouth. I started to gag but he held my head down until I started to swallow what I could. He finally let go of my head and I pulled back with long strand of cum trailing from my mouth to his cock.
I looked at him and said "you were supposed to tell me before you came."
"I know, but it felt so good I didn't want you to stop" Dan said to me.
Dan got up and started getting dressed. I looked up at him and said "what about me? You told me if I sucked yours you would suck mine."
He looked down at me and said "I will tomorrow, but we have to go now, hurry up and get dressed so we can go."
PART-2
The next day around ten in the morning I went down to Dan's house to see what was going on. When I got there he was sitting on the sofa watching a porno flick rubbing his cock. We sat there and watched it for a few minutes and then he asked me if I wanted a beer. I gladly accepted and before I knew it we had drank 2 beers each down.
We sat there watching the porno stroking our cocks when Dan reached over and grabbed my hand and put it on his cock. I slowly started jacking it up and down feeling the firmness of his meat in my hand.
I looked over at him and he smiled at me and said, "come on, suck it, you know you want to".
"No, you lied to me yesterday and never sucked mine" I told him.
"I promise I'll suck yours today but lets have another beer first then I have an idea" he said to me.
We got another beer and we sat on the sofa and drank it. I was slowly stroking his cock and he would stroke mine a few times them stop just to keep me interested. I leaned over and slid his cock in my mouth and started sucking his wonderful meat for about 5 minutes when he stopped me. We finished our beers and when I got up to go use the bathroom I almost fell from the buzz I had.
When I came out Dan was standing inside his parents room which was usually locked. I went in with him and he started showing me all sorts of stuff. Sexy looking bras, panties, teddies, thigh high stockings, dildos and all sorts of other sexy stuff. Apparently his parents were a little on the wild side when it came to sex. I couldn't believe my eyes, I had never seen such stuff except in porn mags.
He threw a pair of red satin panties at me, a red bra, pair of sheer black pantyhose and a black satin nighty that was very short.
I looked at him and ask "what the fuck do you want me to do with these?"
He looked at me with a wicked grin and said "your gonna fucking put it on and suck my cock some more".
"You lost your damn mind if you think I'm wearing that shit" I spouted back.
He started to laugh and said "You'll wear it and do what I tell you or I'll tell everyone on this street your a cockscuking faggot".
I couldn't believe my ears, he was going to black mail me into dressing in girls clothes and sucking his cock. All I could do was stare at the ground.
He looked at me and said "that's what I thought, now go get dressed in Pam's room and come out when your done, I'll be waiting."
I walked into Pam's room and shut the door and sat on the bed looking at the clothes he wanted me too wear. I couldn't believe what was happening. I mean I had snuck into my mom and dads room when I was real young and put on pantyhose like my mom had done and just a year or so ago I took a pair of hose and jacked off in them. The feeling of the nylons on my bare cock was electrifying!
I got undressed and rolled up one leg of the hose and slid my foot in. As I pulled it up to my knee the feeling of the nylons gave me goose bumps. I slid my other foot in the hose and pulled them all the way up. When the nylons touched my cock the feeling was so sensual. I ran my hand up my legs getting the hose tight against my legs and snug on my ass and cock. I picked up the string bikini panties and stepped into them sliding the up and on. I put the bra on how I had seen my mom do it by putting it on backwards then spinning it around then sliding my arms through the straps. It was of course to big since I had no tits so I rummaged around and found some socks to stuff in the cups. I slid the nighty over my head and adjusted it so the bra fit into place under where my tits should be.
I looked into the mirror and couldn't believe my eyes, here I was standing there dressed in womans clothes. I was so nervous I must have lost track of time because I heard Dan say "what's taking you?", "nothing, I'll be right out" I said back. I looked in the mirror and did a spin making the nighty flare out, damn that was sexy I thought to myself. I opened the door and walked out.
When I walked out I didn't see Dan anywhere, I called out , "Dan, where are you?"
"I'm in here in the kitchen" he said.
I walked to the kitchen and he was standing there with a couple of shot glasses filled with booze and smoking a cigarette.
"Damn!, you look pretty good dressed like a girl, here take this shot of whiskey, it will make you relax." he said
"I've never had whiskey before." I said to him.
"Try it you'll like it" he said to me.
"Ok, I'll try one but I already have a buzz and I don't want to get sick or anything" I told him.
He handed me the glass and took his in his hand and raised it like a toast.
"Here's to you, and your sweet mouth" he said with a grin.
We touched glasses and I drank the shot down. It burned as it went down and he handed me a glass of water to chase it with. I drank a few good gulps of water to soothe my throat.
"Wow that burned a little but it was ok" I said to Dan.
He grabbed another beer from the fridge, I told him I didn't want one.
"That's fine we'll share this one while we smoke a cigarette" he told me.
"I've never smoked before" I said to Dan.
He looked at me, smiled and said "today is going to be a day of firsts for you, let's go to the den and watch some porn and you can suck my cock some more."
I turned to walk out and stumbled a bit.